Insanity
by toalltheirown
Summary: The young business tycoon never saw herself as a soccer Mom, however after a spontaneous lunch date with Henry's coach she suddenly finds herself doing everything in her power to attend her son's sessions.
1. Chapter 1

**A/N – My 10 year old brother actually gave me the idea for this fic. I think I know where I want it to go but if you have any ideas of your own go ahead and let me know. It's an AU, so there is no curse or FTL.**

**Disclaimer- I do not own Once Upon A Time or any of the characters. **

**Chapter 1**

Emma made some finishing touches to the promotional flyers, making sure she'd remembered every single detail before printing them off. The college student needed everything to be perfect if she wanted anyone to take her seriously and actually sign their kids up. Emma and her best friend of 3 years were coming to the end of their school year and needed something to keep them busy over the summer, not to mention needing the cash after they were simultaneously fired from the cafe on campus for sleeping on the job.

"Em, are you sure you don't want to name it 'Swan's Summer Soccer School'? I feel like we're missing a big opportunity there," she heard her roommate ask. Her long brown hair blocked Emma's view of the computer as she leaned on her shoulders.

"We're doing this together Ruby, plus it was your idea to begin with, I can't take the credit for that," Emma sighed, the name did have a ring to it but 'Little Strikers' was cute, and was exactly what she hoped to turn the kids into after the six weeks. "And there's too many S'," she dismissed, shaking Ruby from her shoulders.

"Fine, so we cut it down to 'Swan's Soccer School'? Come on Em, it's catchy!" Ruby grabbed the arms of her chair and spun her around, giving Emma her signature puppy dog eyes.

The blonde shook her head and smiled, "You really don't mind?"

"It was my idea to call it that!"

"Ugh fine. If you insist," she huffed, turning herself back to face the computer so she could edit the text.

"Yay!" Ruby clapped her hand like a five year old and began jumping on the bed next to her. "Now hurry up and print those off so we can put them on every solid surface in town," she said in between breathes.

Emma laughed as she printed the last of the flyers. "I can't believe we're doing this,"

"Isn't it great?!" Ruby beamed clasping her hands together as she jumped down.

"What if no one signs up, all of this is a waste of time and money?"

"They're gonna sign up Em. Who can say no to Swan's Soccer School?" she almost sung. "Look, it's something fun to do, and think of how good it will make us look,"

Ruby was right; spending their summer with a bunch of kids would look good for them when it came to extra credit. "Okay, okay," she eventually smiled, handing Ruby the pile of papers.

* * *

It was only two weeks until summer break and the pair still hadn't rounded up enough kids to have a five-a-side game against each other.

"7 kids, Ruby! 7! I knew we should have gone with 'Little Strikers'" Emma flopped on her bed hearing the sound of what could only be more flyers beneath her. She was sick of the sight of them. They had spent the best part of a week pinning them on every lamp post, wall or notice board they could find.

"Relax we have plenty of time to get a couple more kids to sign up," she said, sitting beside her. "The minimum we need is 10, which means we only need 3 more parents to get in touch."

Emma looked up at the brunette who was obviously trying her best to make her feel better, and if she was going to be honest, it was working. Since day one, she couldn't resist that huge smile of hers and her soft brown eyes. "But how do we do that?" she asked pushing herself up on her elbows.

"Okay so the age group we decided was 6-7 right? Well we just change the age, simple as that"

"And that'll work?"

"Probably. Only one way to find out, go change the flyers and I'll ask Mrs Blanchard if her daughter will hand them out to the class she teaches! I was talking to her at a bar the other day and I'm pretty sure she said she taught kindergarten,"

"I'm surprised you can remember," the brunette scoffed.

Ruby noticed Emma was still looking a little disheartened by the lack of numbers they'd gotten so far, so she decided to take it upon herself to whip the blonde back into action. "Let's go, let's go!" she shouted like an army corporal directing their troops, "to the desk, Swan! Move it, move it!" she smirked, grabbing her ankles and pulling her off the bed.

Emma's smile soon reappeared, as she stood up and saluted Ruby, "yes ma'am!" He smile turned into a grin when she turned around placing her hands on Ruby's shoulders. "When did you become the brains?" she teased before dodging a slap on her butt from the brunette.

* * *

"Mommy, look what Miss B gave me!" Regina heard the patter of tiny feet running across the marble floor of her office. She stood from behind her desk to pick up her son who'd just arrived home from school.

"Hi baby," she grinned as she picked the child up. "What do we have here?" She asked taking the flyer from him and resting him on her hip.

"Can I go, pwease?" he mumbled, tangling his fingers in his mothers dark locks.

Regina scanned the flyer noticing the bold red text first; she glanced further down to spot a large soccer ball and a brief paragraph. Perfect. At least this way she wouldn't have to go looking for a babysitter, she didn't have the time or the energy to sit through countless interviews. All in all the class seemed perfectly fine and she found no reason not to let her son participate. Starting at 9 am and finishing at lunch gave her enough time to pick him up on her lunch hour and drop him off with her father who had no problem looking after him for a couple of hours.

"Hm, that depends on if you're a good boy over the next two weeks. If you can manage that, then we'll see,"

The 5 year old took that as a yes and swung his arms around his mother's neck, burying in his face in her hair. "You're the bestest mommy ever," he muttered just loud enough for her to hear. She kissed his cheek before setting him back to the ground with a warm smile.

"Come on, let's go see where your grandfather has gotten to," her grin not leaving her face as he reached up for her hand.

* * *

Regina rushed around the kitchen trying to get together Henry's bag for the day ahead. She finally found the jacket she was looking and called her son into the room so she could finish dressing him. During breakfast Henry had managed to spill his breakfast all over his clothes, meaning she had to bath and dress the 5 year old again, setting them back 30 minutes on her schedule.

"Henry, work with me here," she sighed as the brown haired child struggled to get out of her grip.

"We gotta go!" he wailed, as Regina tugged on the zip of his jacket.

"Yes, I'm fully aware we are running late, that's why you have to let Mommy get you ready,"

"Kay, but then we gotta go," he sighed, allowing his mother to slip on his shoes.

She tied the laces on Henry's sneakers, so they could finally leave. Henry grinned as he took her hand in his and pulled her towards the car. After clipping him into his car seat, she let out a sigh of relief, before looking down and noticing they were already 15 minutes late for the session. _Great. _

Regina instantly regretted wearing heels as her son dragged her across the soccer field. Her heels sinking as she walked, making it incredibly difficult to keep her balance. She noticed a tall, brunette sporting a pair of ridiculously short shorts talking with a group of parents. She next laid eyes on the young woman with a bag full of soccer balls slung over her shoulder, her blonde hair was pulled back into a messy ponytail. Her biceps flexed as she set them down and that's when she promptly averted her gaze as she realised she was staring.

"Hi, I'm Ruby. I take it you're Henry's mom?" Ruby asked with a smile.

"Regina Mills," she extended her arm to greet Ruby, but her eyes soon left hers as she looked around for where her son had disappeared to. "Uh, how did you know?"

Ruby noticed the worried look on her face and quickly reassured her, "he's there," she pointed over to the group of children sat at the blondes feet, almost as mesmerized as she Regina was. "And Henry is the last one to arrive,"

She shook her head out of the daze she'd fallen into and gave Ruby a small smile, "Oh, of course. I'm sorry about that, I was running late. Speaking of running late I really must get going," She said in almost one breath.

"Oh, you're not staying?" Ruby asked looking over her shoulder to make sure Emma still had everything under control.

"I'm afraid not, I have a lot of paperwork to attend to, Miss-"

"Lucas. But please just call me Ruby. Are you sure you're not gonna stay, all the other parents are staying," she signalled towards the small group of stereotypical soccer moms sat on the bleachers.

Regina could use a couple more minutes to compose herself before she got back to the office. She was already half an hour late, what's another 30 minutes to that? She was the boss after all. "30 minutes, that's it. Then I'll have to get back to work," she gave Ruby a genuine smile, pulling out her phone to inform her secretary she'd be even later than she thought.

"Great," Ruby beamed, "you can take a seat with the rest of the Moms,"

Regina nodded before taking her seat on the not so clean bleachers. She continued to watch her son attempt to guide the ball around the cones set out, a proud smile spread across her face. Although her focus wasn't completely on the tiny bundle of energy, it was on the considerably larger bundle of energy, who she assumed went by the name of Miss Swan.

"Okay guys, we're gonna have a little competition," she heard Ruby shout from across the field, "first one to catch Emma get's 5 points for their team!" The unexpected blonde barely had time to uncross her legs from her sitting position when she was tackled to the ground. Regina let out a small laugh, as she watched Henry wrap his legs around hers, refusing to let the coach go before deciding she should head over to the office.

* * *

"Can you believe it? $180! If we keep the numbers up we're gonna be loaded," Emma exclaimed, tucking the money into an envelope in the glove compartment.

"I'll tell you what I can't believe...I can't believe there were no hot, older brothers! Not a single one," she stuck out her bottom lip as she shoved the equipment into the back of Emma's bug, looking unfazed by the amount of money Emma was shutting away.

Emma laughed. "Just get in the car!"

Ruby did as she was told and slid in the passenger seat. "What about Dylan's sister, she was smoking!"

"Ruby, we didn't do this to pick up dates," she laughed looking over at the brunette.

"Yeah but that's the perks of the job," she smirked, stealing Emma's sunglasses from the backseat and sliding them on.

The blonde pulled out into the empty road and drove the pair to Ruby's Grandmothers Diner. They both took a seat opposite the old lady and thanked her as two ice cold glasses of water were placed in front of them.

"So how was the first day?" Granny asked preparing food for the girls.

They both shrugged, gulping down their water in sync.

"Your first honest day's work does tend to tire you out,"

"We worked plenty at the cafe," Ruby bit back almost defensively.

"If I do recall correctly, you were both fired for sleeping on the job. Am I wrong?"

Emma zoned out as the two continued to bicker. The scenes weren't uncommon, as a matter of fact they'd become a daily occurrence. Ever since Granny had refused to hire Ruby the pair had been arguing non-stop.

"Emma!" a tug of her shorts made Emma snap out of the day dream she was currently in. She looked down to see one of the kids who she'd just finished coaching. Emma stood from her seat and knelt down, so she could make eye contact with the boy.

"Hi Henry," she looked around for Henry's Mom but she was nowhere in sight. "Are you he-"

"Henry, don't ever run away like that again!"

Emma's head snapped up, following olive toned legs that met a tight pencil skirt and a snug fitted blazer. Her eye's lingered a second longer than they should have when she noticed the buttoned blouse was showing a slight bit of cleavage.

"I do apologise, he must have seen someone and just-" Regina trailed off before she realised who exactly Henry had spotted. "Oh, Miss Swan," she smiled, flattening her blazer for no apparent reason.

Emma straightened up to greet the woman sheepishly. "Hi," she smiled.

"Again, I apologise if Henry has ruined your lunch he's never run off like that before,"

"No, he didn't. Don't worry about it," she said quickly as she ruffled the child's hair. "Actually I haven't even ordered yet,"

"Mommy can Ems eat with us?" he pleaded.

"I'm sure Miss Swan has better things to do. Come along Henry," she reached out for him and Emma couldn't help noticing how flustered the woman looked.

"Um actually I don't," she interrupted, giving Regina a smile, then looking back down at Henry. "That's if you don't mind?" She asked looking back at the older woman.

"I-uh, sure. Of course," she managed to get out as she stared blatantly at the blonde.


	2. Chapter 2

**Chapter 2**

Ruby arched her eyebrow when she noticed the blonde had disappeared from the seat next to her. She spun around on the bar stool and noticed she was now seated next to a brown haired child. She recognized the boy almost instantly but was still confused as to why she was eating lunch with Henry and his uptight Mother. She caught Emma's eye and shot her a dangerous glare, while the blonde's brows furrowed in confusion.

Just as Ruby was about to signal Emma to meet her in the bathroom and give her the biggest lecture for ditching her without warning, Granny had told her to make herself useful and clean the vacant tables. Of course this lead to another argument after she refused to do so, if her Grandmother wasn't willing to pay her; Ruby wasn't willing to help out.

"So Miss Swan, what desired you to work with children?" Regina asked. She was never one for small talk but she couldn't bear to sit in the awkward silence for any longer.

"It was Ruby's idea actually. We needed the money to keep up with our rent, and we both love kids so," she shrugged, taking a sip of her water. "It's only for the summer though, school starts again in September," she added.

_School?_ The older woman couldn't say she was that surprised, she could tell Emma was young but she had no idea just how young. It almost made her feel guilty for the obvious attraction she felt towards the blonde.

"Ruby's pretty," the child burst out interrupting her train of thought. Both women looked at him before exchanging a soft glance.

"She is," Emma agreed.

"Not as pretty as Mommy though," he grinned lifting his head and looking at Emma. "She's the prettiest. Isn't she pretty?"

"Very," the soccer coach agreed a little too quickly. The comment caused the older woman's cheeks to redden however she couldn't fail to notice the smug smirk on her face. "Quite the charmer you've raised, Mrs Mills."

"_Miss_," she corrected sharply, though her tone was not unpleasant. "It seems I have yes," she went on, "I imagine he'll be a heartbreaker when he's older,"

"Like his Mom?"

Regina shot her a playful glare without responding to the blonde.

"As much as I would love to stay and chat, I should be getting back to work. This was," she thought of a word that could describe their lunch together but the only one that came to mind was spontaneous. She'd barely said a word to the blonde before Henry invited her to join them, which at the time put her in quite an uncomfortable position. It wasn't an ideal situation that was for sure. "Nice," she smiled; it wasn't quite a lie but not the complete truth either.

"Yeah thanks for letting me sit with you guys," she said to Regina.

"It's okay," Henry answered for his Mom, before scrambling over Emma's legs not giving her a chance to slide out of the booth.

Emma let out a soft chuckle, "Will I see you Thursday, Henry?"

"Yup," he nodded enthusiastically.

"And what about your Mom, will I see her too?"

"Mommy?" he asked looking up at his Mom who seemed to be having an intense staring competition with Emma, neither one of them willing to break contact.

"I suppose I can stay for a little while," Regina mused taking hold of Henry's hand. Emma laughed at the reply, giving her an understanding nod.

"Bye Emma," Henry waved with his free hand.

"Yes, goodbye Miss Swan,"

"You know you can call me Emma too,"

"I don't believe we're that well acquainted, _Miss Swan_," Regina was once again wearing that signature smirk of hers, before she turned to leave the Diner.

Emma took her seat back in the booth after the two left. _What the hell was that?_ She tried to ignore every thought that indicated anything other than a nice conversation between two adults. That's all it was, friendly banter, right? But why did she agree to sit with them in the first place?

"What the hell was that?" Ruby mimicked the exact question that was on her mind not 30 seconds ago.

"What?"

"You left me to sit with the kid," she pointed out.

Emma released a small sigh of relief though she had no idea why. It was just lunch. "He begged," Emma shrugged.

"You left me with Granny. Alone. To sit with a 5 year old," _and his Mom_, Emma added silently.

"You should have said no," Ruby continued, accepting her roommate's apologetic smile.

"I'd have to be heartless to say no to that face,"

"Just give a girl a heads up next time yeah?" She grinned, holding out her hand which Emma took willingly. "Now let's get cleaned up and ready to celebrate a successful first day!"

"Let's," she smiled, following the brunettes lead out towards the bug, grateful she hadn't pressed further on the situation because honestly, she wouldn't know what to say. She accepted the offer; they sat in comfortable conversation and then they said their goodbyes. It was as simple as that.

* * *

Regina kissed her sleeping son's forehead then turned back to Kathryn. The blonde quirked her eyebrow as she handed Regina another dress. She scrunched her nose and shook her head in the negative before shooing her best friend out the way of the entrance of the closet. Regina emerged a few moments later holding a vibrant tight blue dress that she found hiding in the back, tags still attached. They'd been looking through her closet for over an hour and had already bored the 5 year old to sleep, Regina was positive Kathryn would be sure to follow if she hadn't picked something out within the last 10 minutes.

"So let me get this straight," Kathryn started as Regina began to undress, "she just invited _herself _to join _you _for lunch?"

"No." She stepped into the dress, and pulled it up in one swift movement, "Henry invited her. Now zip me." Regina motioned towards the zipper on the back of her dress.

Kathryn complied. "And then what happened?"

"Then, we had lunch,"

"Then you had lunch?" the blonde quipped.

"Exactly," she smirked, "Now can you stop being so inquisitive and make yourself useful,"

"I'm your best friend, it's my job,"

"Which one?" the brunette asked, lifting her eyebrow.

"Both," she teased. "What would her Majesty like me to do?"

Regina laughed, placing a hand on her forearm. "Would you carry Henry into his room, my father should be here any second and then we can go,"

With that, the blonde leaned over the bed to carefully lift up the child without waking him.

It was fair to say Regina wasn't used to running late, yet this was the third time today. First was the incident with breakfast, Henry was so focused on being early for his first soccer lesson he ended up spilling his fruit loops down his front, making them both considerably late. Second was after lunch. Regina had been so caught up in conversation with Emma that by the time she'd dropped Henry off with Kathryn she had made herself 20 minutes late for work. And the third, being this very moment. Kathryn had knocked her off schedule with the consecutive questions about who Emma was and why Henry had been talking nonstop about her for the best part of her babysitting duties. Regina quickly noticed a pattern forming; Emma Swan.

* * *

"Regina this is the first time we've been out together since you had Henry, will you please loosen up,"

"I have no idea what you're talking about. I'm having fun," she replied with a shrug.

"The only time you've moved from your seat was to pee, please come and dance with me,"

"Kathryn, you know I don't dance,"

"P-lea-se" she whined, tugging at her hand.

"Now I see where Henry gets his mannerisms from, because _this_," she waved her hands around Kathryn's face, "is all too familiar!"

"Stop changing the subject," she grabbed her hand, her grip tightened as the brunette tried to wiggle her way out of her grip. Now who was acting like the five year old?

"Come," she let out a soft laugh, finally managing to pull Regina towards the dance floor.

After a couple cheesy dance tracks, and a Queen classic the two returned to their seats. Regina's hair was now untamed and her cheeks slightly flustered, however her grin still remained.

"That wasn't so hard was it?"

"No, I suppose not," Regina said breathlessly, apparently she was still slightly out of breath too.

"Good, you can go get the next drinks while I go to the little girl's room. Then we shall return to the dance floor," she sang the last part and shuffled back, previewing some god awful dance moves.

Over at the bar Regina ordered a red wine for herself and whatever concoction of colourful liquids Kathryn was now drinking. As the bartender put on a show, twirling different bottles of alcohol over his head and behind his back, she received a sharp nudge in her side. She assumed it was Kathryn back, already wanting to drag her to the dance floor, but when she turned she was surprised to see Ruby stood with a wolfish grin smeared across her face.

"I thought it was you!" she beamed, clearly well over her daily alcohol intake in fact she was probably over her weekly allowance too. "What's a classy lady like yourself doing in this place, Mrs Mills?"

"Miss," Regina stressed yet again, although she was slightly amused by the rest of the question. "I'm actually with a friend."

"Oh. Right," she winked, nudging her side playfully. "He could have took you to a nicer place than this, am I right? Not to mention letting you buy your own drinks," she scoffed.

Regina's eyes widened, "I'm not on a date, Miss Lucas. I'm here with my best friend, she's just in the bathroom," she was quick to correct.

"What a coinkydink, me too," she grinned pointing over to the back of a blonde, who was grinding against a scruffy looking man, around Ruby's age.

"Is that-"

"Emma...And Graham," the younger brunette finished for her, "If you don't mind, I'm about to go make that twosome a threesome! It was nice seeing you again," she slurred, before bouncing her way over to the centre of the floor.

Her eyes followed Ruby, but somehow snaked their way from Emma's strong calves to the end of her incredibly short red dress. Emma Swan sporting dress? Now that was a sight for sore eyes.

"What're you staring at?"

She shook herself from the gaze Kathryn had rudely interrupted. "What? Nothing, I was waiting for you. What took you so long?"

A blush spread across her cheeks as they watched a muscular blonde emerge from the bathroom. "You didn't?"

"No. God, no. We just, had an extremely hot make out session," she blushed again, taking a sip of her bright blue cocktail.

The ladies opted to stay at the bar for a while. Kathryn hardly said a word; instead her eyes were fixed on the man across the room from her. "I'll be right back," she smiled, standing from her stool.

"No, you're not leaving me," Regina frowned, holding her arm back.

"But-"

"Kathryn, this was your idea in the first place!"

The blonde huffed, slumping back in her seat.

* * *

The night was already turning out to be one of the best she'd had in a while. Emma and Ruby decided to meet up with their college friend, Graham. He'd just moved to America from Ireland to study criminology. They'd hit it off pretty well and the three were practically inseparable during each free break they had together. Tonight though, Graham had suggested a pub crawl and the girls didn't know how fast to accept the offer. All their money had been spent on food, rent and other living essentials the past month, however now they had money to spend.

They were now onto their third bar this one was a lot busier than the previous ones, but it didn't seem to bother the three. Emma continued to dance against Graham as she waited for Ruby to return from the bar with their drinks however when she returned she was empty handed.

"Rubes, where's the drinks?"

"Shit, I must have left them at the bar when I was talking to Regina, my bad,"

"I'll go get them, don't worry." Graham stepped in; making sure his strong accent was heard over the blaring music.

Emma nodded until she processed the words. "Regina?" she asked, eyes widened. "Regina Mills?"

"Duhh," Ruby laughed.

"What? Regina's here? Where?"

Ruby shrugged and faced the bar where Regina was previously standing, "She's ther-wait where did she go? I swear she was there a minute ago?" Ruby looked a little confused. Scratch that, she looked a lot confused. It probably had something to do with the excessive amount of alcohol she'd consumed.

"Are you sure?" she asked not entirely convinced.

"Uh, yeah? I remember. She was wearing a blue dress and was waiting for her friend,"

Emma looked around but the dark haired woman was nowhere in sight. She figured Ruby had drunk a lot more than she'd first thought and was now starting to hallucinate, which is obviously a sign that it was time to take her home.

"Well she's not here now. Are you positive she was here? Maybe it was someone who looked like her?" Emma was pretty sure Regina wouldn't be caught dead in this place.

"No she was here, she couldn't have just disappeared?" Ruby rubbed her head in confusion.

"Well, maybe she left?" She smiled, deciding to entertain the idea of Regina Mills drinking in a rundown pub rather than an uptown champagne bar. "Just like we should be doing, you've had way too much to drink,"

"That I have," Ruby laughed, sliding her arm through Emma's.

* * *

After the pair had parted with Graham who was chatting up the redhead behind the bar, they made their way outside towards Emma's bug. Fortunately she'd only had two drinks so she was perfectly fine to drive.

"Just give me a minute," Ruby said, leaning against the back of the car, looking as though she was about to vomit.

"I swear if you're sick in the bug,"

"I'm sure it wouldn't make that much of a difference to the heap of scrap you call a car, Miss Swan,"

Emma whipped her head up to see Regina stood there, looking as beautiful as ever. The glow from the street lights lit up her face, showing her dark eyes and sinister red lips. She glanced down taking in the blue dress that Ruby mentioned. It hugged her in all the right places; they drifted further down admiring her perfecting toned legs that were complimented by black suede heels. She was sure her jaw had dropped as her eyes looked over the short haired brunette. Emma had almost forgotten about the snide comment she'd made about her car, _almost_.

"Hi," she said when she eventually composed herself. "Uh, what're you doing here?"

"I assume the same thing as you?"

"Well yeah, I mean, uh," she let out a nervous laugh, "I meant what are you doing out here, uh by yourself?"

"I'm waiting for my father to pick me up,"

"Aren't you a little old to be getting a ride home from your dad?"

"Are you calling me old Miss Swan?"

"What no, I meant-"

"I was teasing," she held a hand up to stop the blonde in her tracks. "It seems my original ride home has other priorities."

"Other priorities?" Emma took her eyes off Regina to check on her friend who was now resting her hand on the fence opposite her, puking in the bushes. _That's my girl. _

"Yes, I believe his name was Frederick."

"Ah," she nodded, now understanding the situation in hand.

"I could take you home if you want?" she offered, rubbing Ruby's back.

"That's kind of you Miss Swan, but my Father is probably already on his way,"

"Probably?"

"I do wish you'd stop repeating everything I say but yes, as long as he's had no trouble waking Henry he should be here soon,"

"He shouldn't have to wake Henry when I can drop you off; it's honestly no bother at all,"

Regina let the idea float around for a while before giving her a silent nod. It did seem a shame to wake Henry. She pulled out her phone to text her Father, telling him not to bother.

"Thank you," she gave her a genuine smile then wrapped her arms around herself.

"You might wanna sit in the car, we'll be waiting a while," she said patting Ruby's back.

"I can wait,"

"But you're cold," the blonde persisted.

"I'll be fine Miss Swan,"

Emma frowned removing her red leather jacket. "If you insist on staying out here, at least take my jacket,"

"I said I was fine," she replied firmly.

"Regina,"

"Then you'll be cold,"

Emma forcefully threw out her arm towards Regina. "Just take the god damn jacket!"

A smirk graced her bright red lips. It seemed Regina had met someone almost as stubborn as herself. She resentfully took the jacket but only because she was generally cold and didn't want to catch hypothermia. She shook her head at the triumphant look on the blondes face and leaned against the rusty yellow car. Making sure her dress didn't come into contact with the god awful piece of metal.

* * *

Ruby was sprawled out on the back seat, a soft snore coming from the brunette's lips. They pulled up outside Regina's home and once again Emma found her jaw hitting the floor. _Holy shit._

"You live here?" she asked.

"I do,"

"It's huge," Emma stared, looking like a kid in a candy shop.

"It's a decent size I suppose," she shrugged simply.

"Your bedroom is probably the size of my whole apartment!"

"My bedroom is none of your business," Regina held back a smirk watching the smile fall from the blondes face.

Emma's frown became puzzled. "That's not what I meant,"

"I know what you meant Miss Swan." She chimed before Emma could elaborate. "I appreciate the ride home,"

"Like I said, it was no problem,"

"Well it was a very sweet gesture. Thank you,"

Emma smiled and watched the brunette leave her car. "Do take care of Miss Lucas," she heard.

"Don't worry, she's in good hands."

"Oh I don't doubt that, Miss Swan," she purred before disappearing behind the door.


	3. Chapter 3

**A/N – Apologies for the wait, I had a lot of coursework to catch up on. I'm hoping to get the next chapter up within a week but for now here's chapter 3.**

**Chapter 3**

Emma had been awake since 7:30am which was way too early for her liking, despite having to be out of the apartment in an hour. For some reason she found her mind wandering back to Saturday night's events. It had been five days since Emma come to Regina's rescue - at least that's how she saw it, though she was sure the brunette would strongly disagree. After taking Regina home she had the tedious task of putting Ruby to bed. Honestly it was like babysitting a toddler when she was drunk. She could hardly put together a sentence, not to mention the drooling and constant vomiting. Then she had to deal with the brunette's moodiness the next morning. She wondered if Regina had woken up with a hangover, if she had anyone to cook the ultimate hangover cure for her like she'd done for Ruby. She made it clear she wasn't married to Henry's father but was he still in the picture?

The daydream she drifted into was solely focused on Regina as she spooned some fruit loops into her mouth. She wondered where she worked; it must be well paid going from the size of her house. Or maybe she inherited it and a shit load of money-of course she'd noticed her designer clothes. Oh what she'd give to see her face when she realised she was still wearing her leather jacket. Her trail of thought then wandered to the site of the ever so regal woman in the tattered red material, she even managed to make that look hot.

Ruby threw the bag of soccer balls onto Emma's lap making her empty breakfast bowl fall to the ground with a crash. It looks like she was making a habit out of awakening Emma from her Regina daydreams.

"Are you serious? You've got 20 minutes to get a shower, move!"

"You know, I think I liked it better when I was the Mom," she teased, throwing the bag back.

"Oh Honey, you were never the Mom. Now get that cute little ass of yours into gear, we have to leave soon."

The blonde wore a smirk all the way to the bathroom, were she managed to get ready in record timing. She tied her hair back into a somewhat neat ponytail then went in search of her contacts.

"Hey Rubes, have you seen my spare contacts?"

She barely heard the "Nope," from her best friend over the noise of her turning her room upside down. At this rate she was going to have to settle for her glasses. _Fucking great._ She let out a sigh as she opened the draw and pulled out some thick, black rimmed glasses that she hadn't worn in forever. They weren't ideal for running around a soccer pitch but they would have to do until she could order some replacement contacts.

* * *

"Mommy, how do I look?"

Regina watched, her mouth gaping open, as her son ran into her bedroom wearing his soccer strip and an oversized jacket draped around his shoulders. She'd completely forgotten about it after it was quickly discarded when she arrived home Saturday night.

"Henry darling, where did you get that?"

"Kitchen." He murmured as he struggled to climb on her bed.

That's right; she'd taken it off when she went to get a glass of water. She remembered quite clearly now, the warm feeling inside of her as she pulled the red jacket around her sides once arriving home. The musky aroma brought a smile to her lips. It was a sweet gesture and memories of their playful banter beforehand came flooding back.

She looked back at Henry who was trying desperately to grab her attention. _He must have had it this whole time._ She pulled out her phone and quickly snapped a shot of the five year old, who at this point stood with his hands on his hips, puffing out his chest with a grin that matched Regina's.

"Be careful with it Henry, it's not your property." However if he was to rip it he wouldn't be doing much more damage, in fact he would probably be doing Emma a favour.

"Finders keepers,"

She tapped his nose before standing, "Unfortunately it doesn't work that way. We have to give it back to Miss Swan today,"

"It's Emma's?"

"Yes. She loaned me it when Mommy and Auntie Kat went out on Saturday."

"Auntie Kat was naughty but Emma was nice,"

"You're quite right dear,"

She picked him up and rested him on her side, "Time to go, my little prince. We don't want to be late again do we?"

The brown haired boy scrunched up his nose and shook his head. "I can't wait to see Em and Rubes!" he squealed in her ear, kicking his legs excitedly.

* * *

Henry was the one who spotted Emma first, it seemed he had an eye for it. He wriggled out of Regina's grip and ran over to the yellow bug where Emma was hauling the heavy bags out of the boot of her car.

Emma dropped the last bag with an exaggerated sigh and was about to close the boot when she felt someone tapping her side. She looked down to see an adorable looking Henry wearing her very own jacket. A chuckle unconsciously escaped her lips at the sight.

"Hello you."

"Hello you," he mimicked.

"Ready to play some soccer?"

"Yeah!" He shouted, dawdling over to the ball bag trying to pull one out.

"Henry." A familiar stern voice made Emma almost about turn. "Have you asked Miss Swan if you could take one of those?"

The child looked up at Emma waiting for the go ahead. She nodded and that was all he needed before he pulled the bright blue one out from the bottom of the bag.

Regina looked down at Henry who was struggling to lift the ball out as well as trying to keep the sleeves of Emma's jacket up. "Don't you think it's time to give Miss Swan her jacket back?"

"Nope, s'mine now!" He said crossing his arms and sticking his tongue out in Emma's direction.

"Henry." She warned.

"Okay," he huffed, shrugging the jacket off his shoulders and giving it to the blonde.

Emma ruffled his hair, trying to pick up his mood. "Thanks for taking good care of it, kid."

"S'okay." He said with a little smile before running off with the ball to join Ruby and a couple of others on the field.

With Henry gone Regina's full attention was now on his soccer coach. _Those are new._ She had no idea Emma needed glasses, then again why would she? They'd known each other less than a week and had only spoken to one another for little over than an hour in total. However she wasn't against the glasses, in fact they were working in her favour. She gave Emma the once over taking in the sight of her bare legs then set her eyes back to the green ones opposite her.

Emma spoke first after visibly squirming under Regina's stare. "Fancy seeing you here."

"Considering it's all Henry's spoke about since Saturday, I felt obliged."

"Is that so?"

"He practically dragged me out of the house this morning." She lied. Though he was excited to see Emma and Ruby it was Regina's idea to leave early.

"Are you surprised? Swan's Soccer School is the bomb," she puffed out her chest in a similar way to her five year old earlier that morning.

She decided to ignore the blonde before noticing Emma reach for the bags behind her. "Would you like some help?"

Emma shook her head, "Are you kidding, I can't let a lady do heavy lifting!"

Regina snorted and Emma was sure it was the cutest thing she'd ever heard. "How very sexist of you, Miss Swan."

"Well, I mean, I wouldn't want you to get that lovely dress all muddied up," she lifted the bag onto her shoulder and smiled. "Besides these are _really_ heavy, I'd be surprised if you could carry them."

"Do you always insult the people that are paying your bills?"

"Not always, you must be special." She smirked as she begun to walk across the field. She noticed more and more people filling the bleachers and decided it was time to get over there before Ruby went all Momma bear on her again. She couldn't face a repeat of this morning.

She heard the clicking of heels behind her and raised her eyebrow again. "Don't you have work?"

To Emma's surprise the brunette told her she'd arranged to have the morning off and would be staying for the full session today. The blonde then replied with some snarky comment about how she should wear more sensible shoes for walking across grass in. It humoured her thinking of how small she would be without her four inch heels.

Regina sat with a proud smile on her face for the duration of the two hour session. Seeing Henry running around without a care in the world always warmed her heart, even more so seeing him climb Emma like a jungle gym. The growing attraction she had for the blonde was even stronger seeing her interact with Henry.

As she watched the children help Emma and Ruby put away the equipment she thought of the next time she'd see the blonde. Two days really wasn't that long to wait but these ten minute meetings were awfully short lived and definitely not enough time to get to know her. She enjoyed Emma's company and would love to get to know her some more.

Would it be weird to ask her to join them for lunch again? Of course it was, she barely knew the woman. But wasn't that the idea, for her to get to know Emma? This was crazy, why was she over thinking this, it's not like she hadn't done it before.

Regina toyed with the idea some more before deciding not to go through with it. She had a lot to get done and stopping for lunch wasn't an option if she wanted to finish by her deadline or that's the excuse she was going with. So instead she dropped Henry off with her parents and headed straight to work.

* * *

Regina was over her head in paperwork when her phone vibrated making her jump out of her skin. She looked down at the message preview and shook her head then unlocked the phone.

**Hey girl! You up for dinner tonight?**

**Oh so you can actually leave Frederick for more than half an hour?**

**Very funny Gi.**

**Don't call me that. Plus I'm still mad at you for leaving me. **

**Still?! That was like last week, come on I'll pay. Pretty please?**

**Fine, but don't make it too late I can't keep relying on my Father to look after Henry. **

**You got it, see you after work. **

Regina set her phone back down and continued with the paperwork for planning permission. Hopefully this time she wouldn't be turned down, she was already pushing her luck with the time schedule the last thing she needed was to be denied for a third time.

* * *

Regina kicked off her heels rather ungracefully and collapsed in a heap on her bed. She didn't even have the energy to remove her dress. She had no idea what time it was but she was positive it was well into the early morning. After coming home, Henry was a bundle of energy and wouldn't sit down for more than five minutes before disappearing into another room of their home. This then turned into a game of hide and seek until he became too tired to find a good hiding place and settled for under his quilt. Not even an hour later he woke up from a nightmare and refused to go back to bed until she read him his favourite bedtime story.

All in all the night had been rather tiresome. On their dinner date Kathryn had spoken about nothing other than Frederick and his plans on opening a gym which she was more than happy to donate money towards _and_ how they'd already talked about moving in together, how could she forget that one? In all honesty it felt a bit rushed, they'd known each other for ten minutes and already had plans for the future. She hardly knew him, he could be swindling her out of her inheritance and she wouldn't have the slightest idea.

They did however move onto the subject of Regina's love life on the drive home. Sometimes she was worse than her Mother.

"_I can set you up with one of Freddy's friends if you'd like. He introduced me to this tall brunette who seemed just your type and she was a fitness freak! Imagine the bod." She said in a hushed tone. _

_She had to fight the impulse to roll her eyes at the statement. "I'm fine."_

"_Come on, you need to get back into the pond. You're not going to find someone burying your head in work."_

"_Things are just fine how they are. Henry and I are a good team, we don't need anyone ruining that."_

"_Okay, okay. But if you change your mind, just let me know. I think her name was Riley or Ruby, something beginning with an R."_

_Regina almost chocked on her lemon water. Leggy brunette who was a fitness fanatic, of course it was Ruby. She laughed at the idea, where had she possibly gotten the idea that Ruby was her type? "Ah yes, I think I've already had the pleasure of meeting her."_

"_And?"_

"_And she's definitely not my type." She scoffed._

"_Really? Because last time I checked anyone with a vagina was your type. When did you get so picky?"_

"_When I became a mother." Regina replied in a light tone._

**A/N – I'm aware there isn't much SQ interaction in this chapter, it was kind of a filler chapter on Regina's part. You'll also get to know a little more about her job in the next chapter, as well as a lot more interaction with Emma.**


	4. Chapter 4

**A/N – I can't thank you enough for the follows and favourites, I know it's such a cliché but it really does keep me going. **

**Just another reminded, I do not own OUAT or any of their characters.**

**Chapter 4**

Emma watched in awe as the small group of kids who could barely kick a ball in a straight line at the beginning of last week, dribbled in and out of the set cones. Who would have thought they'd make this much progress in three sessions. After a thorough warm up Emma directed them to the goal line, while Ruby stayed at the edge of the 18 yard box.

She clapped her hands enthusiastically to grab the group's attention. "Okay, time for a little game we like to call 'What's the time, Miss Wolf?'"

She laughed at a couple of childish squeals, and then carried on. "Now have any of you played this game before?"

The children in front of her shook their heads in unity, "Great, so here's the deal,"

"We're gonna start on the goal line and the aim of the game is to be the first one past Ruby. However Ruby isn't Ruby anymore –"

"She's Miss Wolf!" Roland shouted at the top of his lungs. Roland was one of Emma's favourites from the group. She knew it was wrong to choose favourites but the kid could do nothing wrong in her eyes, even if it was shouting out when she specifically told them not to at the start of every session. Damn those adorable dimples.

"Exactly! Ruby is now the big bad wolf and if we want to take a step forward we have to ask her 'What's the time, Miss Wolf?' This is when the _wolf_ will reply with a time and that's how many steps we're allowed to take,"

"But that's not fair Ems, you have longer legs!" Henry pouted. He was too clever for his own good, just like his Mother.

"Good point kiddo, but you didn't let me finish. If Rub- I mean the wolf, if the wolf decides she's hungry she'll shout 'dinner time' and that's when we have to run for our lives! If she manages to catch you before you cross the 18 yard line, you're outta here!"

"Oh so because you have longer legs you'll be closer to the wolf when she says 'dinner time'?" One of the older kids asked.

"Man you kids are smart, are you sure you haven't played this before?" They shook their heads in the negative once more before Emma told them to get ready.

"Ready? On three. One, two…"

"What's the time, Miss Wolf?" They shouted in unison.

"3 o'clock!" Ruby yelled back, watching them take three large steps towards her.

"What's the time, Miss Wolf?"

"7 o'clock!"

As the children started getting closer, their large steps were becoming increasingly smaller. Emma and Ruby shared a smirk, signalling for what was coming next.

"What's the time, Miss Wolf?"

Ruby paused for effect before showing her perfectly white teeth in a large grin. "Dinner time!" She set off at a sprint, chasing the group inside the box. As it was their first time playing she decided to go easy on them and let them all across the line, all except Emma that was. She chased down the blonde like a wolf would its prey, earning a few screams from the children behind her. She wrestled Emma to the ground, pinning her down by her shoulders. "Gotcha Blondie!"

The kids cheered when Emma finally stood up from the blow. "That was so unfair, I was protecting Henry!" She said in her defence. "It's your fault I was eaten by the big bad wolf!" She laughed, pointing a finger at the five year old.

Henry stuck out his tongue and Emma returned the gesture, all under the eye of his very observant Mother who found herself completely mesmerized by their playfulness. She held a breath as Emma swept Henry into her arms and spun him around. "Next time it's every man for themselves! You're on your own kid." She said, setting him down carefully on the ground.

Ruby split the group off into two teams before noticing they were a player short. "Okay because Spencer is sick, Emma will be keeper for the red team! Go put on your bibs then take a break, kick off's in three!"

As the morning grew closer to midday, the scorching sun gave the blonde a radiating glow. Regina watched on as she took a drink from her bottle and wiped her brow with the bottom of her tee, showing just enough skin for her to see the bottom of her toned abs. And to top it off, it looked like the glasses were staying. When she realised she was staring profoundly, she reverted her eyes back to Henry and smiled softly at the sight of him high fiving a small wavy haired boy.

The swarm of blue coloured bibs gathered around Emma's feet, teasing her about the amount of goals she conceded. She folded her arms and sat down in a faux huff.

"Alright, alright! Leave Em alone you guys!" The brunette laughed. "Oh and don't forget we're choosing your positions next session for your first friendly so make sure you're here!" With that, the children scrambled to their feet and ran off to greet their parents.

* * *

Emma sat at the bar nursing a beer while her best friend attempted to flirt her way into the barmaid's pants. Their afternoon consisted of pizza and monopoly so Ruby figured the only cure for their agonizing boredom was to go out. This was the second weekend running they had spent their night at The Rabbit Hole. It seemed Ruby had taken a liking to the brunette behind the bar; Emma was surprised she remembered her, the state she was in the previous weekend. Normally she wouldn't have minded the fact that Ruby had ditched her but Graham had also disappeared early into the night, thus she was left alone to harbour her thoughts.

"Is this seat free?" A strong Irish accent cut through the usual dull drawls around her. Emma looked up from her beer to see a dark haired man dressed head to toe in leather. He was a sight, that's for sure. His eyeliner stood out even in the shadows of the poorly lit bar-she never really understood the whole guyliner craze.

"It's all yours," she replied with a nod.

He took the seat and smiled. "Can I buy you another drink?" He offered.

"Nah, I'm good thanks."

"Come on, you look like you could use one?"

"I still have half a bottle, thanks anyway." She wasn't in the mood to entertain the guy but she couldn't blame a trier.

"Maybe later, say Tuesday?"

"Look buddy, I'm really not interested."

"Killian, the name's Killian." He smiled, resting an arm on the bar.

"Look _Killian_, sorry but I'm just not interested." The more this guy spoke, the more she had an urge to punch him in the face. There was nothing wrong with being a little persistent, who doesn't love a chase? However she'd made it very clear the guy didn't stand a chance so why couldn't he just be on his way?

"That's what they all say. Don't worry, much hotter woman have been broken down by my charm." He smirked, taking a sip off his rum.

This was the perfect chance to wipe that sickly smirk off of his ugly face. "Same here, man. The ladies always succumb to the Swan's charm."

Sure enough, a confused eyebrow shot up. "What do you mean?"

"Well, I'm gay."

"Oh," he said, stunned by her boldness. "But didn't you hear? I'm the cure for lesbianism." He said in an all too arrogant tone.

"Right, yeah I totally see it." Emma laughed. It was guys like him that made her physically sick to the stomach. "If you don't mind I'm gonna go." She said, already up from her seat.

"Your loss." He shrugged, already searching the crowd for his next victim.

Emma simply rolled her eyes and made her way to the restroom. She pushed open to door and let out a sigh. "What an ass." She muttered to herself as she studied her face in the grubby mirror. She could probably leave right now and neither friend would notice. Ruby was too busy drooling over Belle whilst Graham was bound to be following some poor girl around like a lost puppy. "Why am I still here?" She asked herself, running her fingers through her hair.

Regina heard a voice from outside the stall and was almost positive on who it belonged to. When she emerged she saw the blonde staring at herself in the mirror opposite. "Miss Swan?" She asked, just to make sure the small amount of alcohol she'd indulged in hadn't corrupted her line of vision.

Emma almost jumped out of her skin, she could have sworn the restroom was empty. "Holy shit!" She said with a hand covering her heart. She felt it pound against her pale hand when she noticed who had just vacated the end stall. "Jesus Christ Regina, you really need to stop sneaking up on me. My heart can't take much more."

"I assure you there was no sneaking." She smiled.

Emma stood up straight, compelled to look somewhat poised in Regina's presence. The brunette resplendent in a tight black dress, whereas Emma was dressed slightly more casual in her jeans and same leather jacket she so kindly lent Regina. "Well what were you doing hiding in here?"

"I wasn't hiding, I was using the bathroom. That is what they're for." She mocked, offering her a coy smile. "What are _you_ doing hiding in here?"

"I believe his name is Killian. Tall, dark, kind of creepy looking."

Regina nodded, making her way towards the blonde. "We've met. Quite the character isn't he?"

"You could say that. The guy wouldn't take no for an answer."

Regina gave her a small smile before moving past her, towards the door. "If he gives you any more trouble, send him my way Dear. I can guarantee he'll leave you alone if I threaten the man with his job."

"He works for you?"

"Indeed." She nodded with a displeasing look on her face. "He worked for my Mother before I took over the family business. She insisted of him keeping his job, but I'd be happy to fire his leather covered ass." She said with a smirk as she watched Emma's facial expressions falter.

"So you're kind of a big deal then?" Emma asked, taking into account that her house was bigger than her entire apartment block and that was probably a result of owning her own business. "What is it that you do?"

"Not that I don't want to continue with this conversation but I'm sure Kathryn and Frederick will be wondering about my whereabouts."

"Ah so you're third wheeling too?"

Regina let out a soft chuckle and Emma was sure it was the most beautiful sound she had ever heard. "It looks that way. Kathryn and I were supposed to be spending some time together but he turned up no later than 20 minutes after she'd left the apartment. They're like a couple of love sick teenagers," she sighed deeply.

"Then how about we grab a couple more drinks and continue the conversation outside?" She asked hopefully. Regina's company was way better than sitting on her own, besides their friends probably wouldn't have noticed either of them were missing anyway.

Full lips pursed then grew into a disarming beam. "I could think of worse ways to spend my Saturday evenings." Maybe tonight wasn't going to be as bad as she originally thought.

Emma slid past the brunette in a similar way to how Regina had done only minutes before. Except this time her arm brushed against her stomach, unintentionally of course. "I'm gonna take that as a yes." She said, opening the door for Regina. It wasn't so much as a chivalrous act, just polite as Emma often was.

* * *

Emma returned to the table with a cold beer and a glass of the bar's finest red wine. Although fine wasn't a good term to use, more like mediocre.

"So," she seemed hesitant before asking. She didn't wasn't to seem nosey or off putting by bombarding her with questions, however she was intrigued to say the least. "You own your own business? That's pretty cool."

"Yes Miss Swan, I suppose it is 'pretty cool',"

"So what exactly do you do? Actually wait let me guess," she thought back to the recent outfits she'd worn over the past two weeks. All were extremely business-y so she doubted Regina was a labourer. "Uh, let's say an accountant?" She smiled, taking a stab in the dark.

"Do I really look that boring to you?" She teased. "You know what, don't answer that."

Emma shot her a cheeky grin, then took a sip of her drink. "Okay, so you're not an accountant. Do you own your own line of hotels?"

Regina shook her head and waited for her to guess again. It was bound to be another incorrect presumption.

"Um, do you work in real estate?"

"Close."

"I give up, you're gonna have to just say it." She laughed, throwing her hands up.

"I own an Interior Design company."

That's when Emma got it. "Mills? How did I not get that before?" She paused. "Wait, you own the largest design company in Maine?"

"Not just Maine, Dear."

"That's so cool. Have you done anything for any hot celebs? I bet you have!" She asked, resting her head on her hands, almost childlike. Regina thought it was extremely cute.

"Of course," she gloated.

"Spill?" Emma grinned.

"Well, when my Mother was in charge and I was around your age Nicole Kidman asked specifically for I to design her daughter's bedroom. That was my first real chance to make a name for myself in this industry. A few months later I got a call from her assistant asking if she could make an appointment for us to co-design her new house. It was awfully surreal."

"That's awesome. I had no idea."

"Well why would you?"

Emma shrugged, "I buy these celebrity magazines, the name Mills is in their more often than not. I never clicked."

"Well now you know, Miss Swan."

"Emma." She corrected for what was due to be the 10th time since meeting her. "I think we're acquainted well enough for you to use my first name, don't you?"

She hummed into her wine glass, earning a complaint from Emma.

"If you keep calling me Miss Swan, I'll be forced to call you by Miss Mills,"

Regina smirked, a roguish expression on her face. "I like that. You make it sound as if I hold some form of authority over you."

Emma sat speechless, not able to conjure up a reply.

"Same again?" The brunette said casually, before waltzing off to the bar.

**A/N – I don't really know what to think of this chapter, I didn't want it to feel rushed or anything so if you could let me know what you guys think I'd really appreciate it!**


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